Photoisomerization-induced patterning of ion-pairing materials based on anionic azobenzene and its complex with a fluorescent π-electronic system

Yamakado, Ryohei; Kitamura, Issei; Hara, Mitsuo; Nagano, Shusaku; Seki, Takahiro; Maeda, Hiromitsu

doi:10.1039/d0cc07640f

Cited by 7 publications

(4 citation statements)

References 31 publications

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“…Pairing PBs with such photoresponsive polymers results in another photoresponsive material. The Marangoni flow and fluorescence patterning of 27a are triggered by the change in surface tension due to the photoisomerization of 26c − in the presence of N ‐alkylpyridinium‐appended polymer [40] …”

Section: Photoresponsive Ion Pairs Comprising Photoisomerizable Unitsmentioning

confidence: 99%

“…The Marangoni flow and fluorescence patterning of 27a are triggered by the change in surface tension due to the photoisomerization of 26c − in the presence of N-alkylpyridiniumappended polymer. [40] Adjusting the numbers and lengths of the aliphatic chains attached to azobenzene offers tunable photoresponsivity. Azobenzene with a carboxylate and an aliphatic chain as an ion pair TBA þ -29 − forms a [1 þ 1]-type complex with 27a (Figure 13a).…”

Section: Photoresponsive Ion-pairing Assemblies Including Anion-respo...mentioning

confidence: 99%

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Photoresponsive ion‐pairing assemblies

Haketa,

Sengupta,

Maeda

2023

Responsive Materials

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This review provides an overview of the π‐electronic ion pairs and assemblies that demonstrate photoresponsive behaviors through photoisomerization and photoinduced electron transfer. Various ion pairs arise from the incorporation of ionic substituents to photoisomerizable π‐electronic systems, such as azobenzene and diarylethene moieties, and their association with counterions. Conversely, numerous ion pairs, made up of positively and negatively charged π‐electronic systems serving as electron acceptor and donor units, respectively, are prepared through ion‐pair metathesis. In both scenarios, the design and synthesis of charged π‐electronic systems play a crucial role in ion‐pairing assemblies. Moreover, the structures and properties of these assembled entities are influenced by the inclusion of accompanying counterions. These ion pairs display photoresponsive actions, including phase transitions through photoisomerization and the emergence of excited‐state radical pairs due to photoinduced electron transfer. Notably, π‐stacked ion pairs (π‐sips) composed of charged porphyrins transform into π‐stacked radical pairs (π‐srps) upon photoexcitation. Multiple components, as oppositely charged π‐electronic systems associated by noncovalent interactions, possessing varying electronic states and traits are suitable for switching behaviors in response to external stimuli.

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Section: Photoresponsive Ion Pairs Comprising Photoisomerizable Unitsmentioning

confidence: 99%

Section: Photoresponsive Ion-pairing Assemblies Including Anion-respo...mentioning

confidence: 99%

Photoresponsive ion‐pairing assemblies

Haketa,

Sengupta,

Maeda

2023

Responsive Materials

Self Cite

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“…13 Methods that utilize light to pattern surface features are of particular interest because light provides a simple, clean and non-invasive stimulus for manipulating matter. 14,15 Traditional ultraviolet (UV) photolithographic based indirect subtractive LCP patterning may be possible in conjunction with plasma etching, however incorporating an appropriate mask material that can be both deposited and sacrificially removed without impacting the material quality or alignment is a challenge and this approach does not appear to have been presented in the literature. Direct UV photolithography of an LCP was demonstrated by Yamashita et al, 16 however the yield was limited and optimal crosslinking required elevated temperature.…”

Section: Introductionmentioning

confidence: 99%

Optical control of alignment and patterning in an azobenzene liquid crystal photoresist

et al. 2023

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“…[13] To date, azobenzene-based materials have received wide attention due to their incomparable functions and widespread applications. [14][15][16][17] Azobenzene-containing -conjugated polymers have high photoisomerization abilities and efficiencies because trans-to-cis isomerization of the azobenzene unit in the conjugated polymer backbone can significantly affect the geometry of the polymer backbone. Consequently, they are commonly distinguished as promising optoelectrical materials.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Discrete Conjugated Fluorene‐Azo Oligomers for the Investigation of Azobenzene Position‐Dependent Physical Properties and Photoresponsive Behavior

Liu

Shi

et al. 2021

Macro Chemistry & Physics

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It is well known that macromolecular structure, including composition, topology and sequence, significantly determines the properties of conjugated polymers/oligomers. To accurately understand the structure-induced properties, discrete oligomers/polymers with molecularly defined structures are the ideal model because they provide distinct nonstatistical results. Herein, a series of discrete conjugated fluorene-azo oligomers with different positions of the azobenzene units along the main chain (i.e., sequence) are efficiently prepared based on CuAAC "click" chemistry via a stepwise chain-growth strategy. Position-dependent behavior has an evident impact on the properties of oligomers, such as thermal properties, optical properties and photoresponsive behavior in both solution and thin film states. In addition, the fluorene-azo oligomers show less photodegradation of 9,9-dioctyl-fluorene in the solid-state than oligofluorene during UV light irradiation; however, position-dependent photodegradation is found in solution. Optimized configurations and UV-vis absorption spectra of fluorene-azo oligomers are calculated by density functional theory. Experimental results and theoretical analysis indicate that the location of azobenzene can play a dominant role in determining the properties of fluorene-azo oligomers resulting from sequence-mandated conformational changes. Undoubtedly, this work can provide deeper insight into the structure-property relationships based on precisely sequence-defined polymer structures.

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Photoisomerization-induced patterning of ion-pairing materials based on anionic azobenzene and its complex with a fluorescent π-electronic system

Abstract: Large mass transport driven by the difference in the photoisomerization-induced surface tension was demonstrated in ion pairs of anionic azobenzene and a cationic polymer. This material motion enabled the fluorescence...

Cited by 7 publications

References 31 publications

Photoresponsive ion‐pairing assemblies

Photoresponsive ion‐pairing assemblies

Optical control of alignment and patterning in an azobenzene liquid crystal photoresist

Synthesis of Discrete Conjugated Fluorene‐Azo Oligomers for the Investigation of Azobenzene Position‐Dependent Physical Properties and Photoresponsive Behavior

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